Diethyl Ether → HCID 23681332, compound

HRID 2296482Notes

Reaction equation

HRID 2296482 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:23]([OH:25])=[O:24].[OH-].[Na+:27].CCOCC>CN(C)C=O>[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:22])[C:18]([CH3:20])([CH3:21])[CH3:19])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:23]([O-:25])=[O:24].[Na+:27]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 13060574HCID 13060574, compound

Product 1

HCID 23681332HCID 23681332, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Oxo-10-(pivalamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid (3.06 g) was suspended in N,N-dimethylformamide (60 ml). To this suspension was added dropwise sodium hydroxide solution (sodium hydroxide 0.36 g in water 1 ml and ethanol 7 ml) at ambient temperature to give a clear solution. After 30 minutes, ether was added and the precipitated crystals were collected by filtration and washed with ether. The crude crystals were dissolved in water (150 ml) under heating. The solution was filtered to remove insoluble materials, diluted with acetone (800 ml), and allowed to stand at ambient temperature. The crystals were filtered, washed with acetone, and dried to give sodium 4-oxo-10-(pivalamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (1.73 g).

Workup

  1. customto give a clear solution
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with ether
  4. dissolutionThe crude crystals were dissolved in water (150 ml)
  5. temperatureunder heating
  6. filtrationThe solution was filtered
  7. customto remove insoluble materials
  8. additiondiluted with acetone (800 ml)
  9. customto stand at ambient temperature
  10. filtrationThe crystals were filtered
  11. washwashed with acetone
  12. customdried

Sources & evidence

ORD record
ord-bb7faabc23e44bc9be6816258137849b
Source dataset
uspto-grants-1984_01
Patent number
US04429126

Reaction notes

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